Heterocyclic compound, organic light-emitting device comprising same, manufacturing method therefor, and composition for organic layer

Abstract

The present specification relates to a heterocyclic compound represented by Formula 1, an organic light emitting device comprising the same, a method for preparing the same, and a composition for organic layer.

1 . A heterocyclic compound represented by Formula 1 below: 
       
         
           
           
               
               
           
         
         wherein, 
         one of X1 and X2 is 0 or S, and the other is a direct bond, 
         L1 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, 
         m is an integer from 0 to 5, and when m is 2 or more, each L  1  is the same as or different from each other, 
         R1 to R13 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. 
       
     
     
         2 . The heterocyclic compound according to  claim 1 , wherein Formula 1 is represented by Formula 1-1 or Formula 1-2 below: 
       
         
           
           
               
               
           
         
         wherein X1, X2, L1, R1 to R13, and m are the same as defined in Formula 1 above. 
       
     
     
         3 . The heterocyclic compound according to  claim 1 , wherein any one of R1 to R13 is represented by Structural Formula A or Structural Formula B below: 
       
         
           
           
               
               
           
         
         wherein, 
         L2 and L3 are the same as or different from each other, and are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, 
         n is an integer from 0 to 5, and when n is 2 or more, each L2 is the same as or different from each other, o is an integer from 0 to 5, and when o is 2 or more, each L3 is the same as or different from each other, p is an integer from 0 to 3, and when p is 2 or more, each R14 is the same as or different from each other, 
         R14 to R23 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. 
       
     
     
         4 . The heterocyclic compound according to  claim 3 , wherein Structural Formula A is represented by any one of Structural Formula A-1 to Structural Formula A-4 below: 
       
         
           
           
               
               
           
         
         wherein, 
         R31 to R46 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and 
         L2, L3, R14, R19, n, o, and p are the same as defined in Structural Formula A above. 
       
     
     
         5 . The heterocyclic compound according to  claim 3 , wherein R19 is represented by any one of Structural Formula A-5-1 to Structural Formula A-5-5 below: 
       
         
           
           
               
               
           
         
         wherein, 
         X3 is N or CRa, X4 is N or CRb, X5 is N or CRc, X6 is N or CRd, and X7 is N or CRe, 
         Y is 0 or S, 
         R51 to R55, R61 to R75, and Ra to Re are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, 
         q is an integer from 0 to 3, and when q is 2 or more, each R73 is the same as or different from each other, r is an integer of 0 to 3, and when r is 2 or more, each R74 is the same as or different from each other, s is an integer from 0 to 2, and when s is 2, each R75 is the same as or different from each other. 
       
     
     
         6 . The heterocyclic compound according to  claim 3 , wherein any one of R3, R4, R10, R11, and R13 of Formula 1 is represented by Structural Formula A or Structural Formula B above. 
     
     
         7 . The heterocyclic compound according to  claim 1 , wherein Formula 1 is represented by any one of the compounds below: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         8 . An organic light emitting device comprising,
 a first electrode;   a second electrode provided to face the first electrode; and   one or more organic layers provided between the first electrode and the second electrode,   wherein at least one of the one or more organic layers comprises the heterocyclic compound according to  claim 1 .   
     
     
         9 . The organic light emitting device according to  claim 8 , wherein the one or more organic layers further comprises a heterocyclic compound represented by Formula 2 below: 
       
         
           
           
               
               
           
         
         wherein, 
         L4 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, 
         R81 to R85 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, 
         t is an integer from 0 to 3, and when t is 2 or more, each R81 is the same as or different from each other, u is an integer from 0 to 3, and when u is 2 or more, each R82 is the same as or different from each other, v is an integer from 0 to 5, and when v is 2 or more, each L4 is the same as or different from each other. 
       
     
     
         10 . The organic light emitting device according to  claim 9 , wherein Formula 2 is represented by Formula 2-1 or Formula 2-2 below: 
       
         
           
           
               
               
           
         
         wherein, 
         L5 and L6 are the same as or different from each other, and are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, 
         w is an integer from 0 to 5, and when w is 2 or more, each L5 is the same as or different from each other, x is an integer from 0 to 5, and when x is 2 or more, each L6 is the same as or different from each other, 
         R91 to R100 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and 
         R81 to R84, L4, t, u, and v are the same as defined in Formula 2 above. 
       
     
     
         11 . The organic light emitting device according to  claim 9 , wherein the heterocyclic compound represented by Formula 2 is any one selected from compounds below: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         12 . The organic light emitting device according to  claim 8 , wherein the one and more organic layers comprises a light emitting layer, the light emitting layer comprises a host material, and the host material comprises the heterocyclic compound according to  claim 1  and a heterocyclic compound represented by Formula 2 below: 
       
         
           
           
               
               
           
         
         wherein, 
         L4 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, 
         R81 to R85 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, 
         t is an integer from 0 to 3, and when t is 2 or more, each R81 is the same as or different from each other, u is an integer from 0 to 3, and when u is 2 or more, each R82 is the same as or different from each other, v is an integer from 0 to 5, and when v is 2 or more, each L4 is the same as or different from each other. 
       
     
     
         13 . The organic light emitting device according to  claim 8 , wherein the organic light emitting device further comprises one or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. 
     
     
         14 . A composition for organic layer of an organic light emitting device comprising a heterocyclic compound according to  claim 1  and a heterocyclic compound represented by Formula 2 below: 
       
         
           
           
               
               
           
         
         wherein, 
         L4 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, 
         R81 to R85 are the same as or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a nitro group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C6 to C60 aryloxy group; —P(═O)R101R102; -SiR101R102R103; and -NR101R102, or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle, wherein R101, R102, and R103 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, 
         t is an integer from 0 to 3, and when t is 2 or more, each R81 is the same as or different from each other, u is an integer from 0 to 3, and when u is 2 or more, each R82 is the same as or different from each other, v is an integer from 0 to 5, and when v is 2 or more, each L4 is the same as or different from each other. 
       
     
     
         15 . The composition for organic layer of the organic light emitting device according to  claim 14 , wherein the weight ratio of the heterocyclic compound according to  claim 1 , the heterocyclic compound represented by Formula 2 is 1:10 to 10:1. 
     
     
         16 . (canceled) 
     
     
         17 . (canceled)